Why Did Rory And Dean Break Up The First Time? - Kidzworld

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Quiz! Stars Hollow Trivia Why did Rory and Dean break up the first time? Courtesy of The WB. Lorelai pressured Rory into dumping Dean, saying she would break his heart if she let it wait until she headed off to college. Dean's been jealous of Jess from the moment he moved to town. His paranoia got the better of him and they broke up. Rory dumped Dean when he told her he loved her and she wasn't ready to say it back. Rory dumped Dean when she caught him cheating with the check out girl at the grocery store. ×

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